linzagolix   Click here for help

GtoPdb Ligand ID: 12283

Synonyms: KLH-2109 | KLH2109 | OBE-2109 | OBE2109 | Yselty®
Approved drug
linzagolix is an approved drug (EMA (2022))
Compound class: Synthetic organic
Comment: Linzagolix (KLH-2109) is an orally bioavailable gonadotropin-releasing hormone (GnRH) receptor antagonist [5]. It was developed for potential to downregulate the hypothalamic pituitary-gonadal axis to inhibit the driving force of LH and FSH on estrogen release, as a mechanism to combat the symptoms associated with endometriosis [6], heavy menstrual bleeding or uterine fibroids [1,4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 147.57
Molecular weight 508.06
XLogP 3.96
No. Lipinski's rules broken 0
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Canonical SMILES COc1cc(F)c(cc1OCc1c(OC)ccc(c1F)F)n1c(=O)[nH]c2c(c1=O)c(sc2)C(=O)O
Isomeric SMILES COc1c(c(c(cc1)F)F)COc1c(cc(c(c1)n1c(=O)c2c(scc2[nH]c1=O)C(=O)O)F)OC
InChI InChI=1S/C22H15F3N2O7S/c1-32-14-4-3-10(23)18(25)9(14)7-34-16-6-13(11(24)5-15(16)33-2)27-20(28)17-12(26-22(27)31)8-35-19(17)21(29)30/h3-6,8H,7H2,1-2H3,(H,26,31)(H,29,30)
1. de Lange ME, Huirne JAF. (2022)
Linzagolix: an oral gonadotropin-releasing hormone receptor antagonist treatment for uterine fibroid-associated heavy menstrual bleeding.
Lancet, 400 (10356): 866-867. [PMID:36116467]
2. Donnez J, Taylor HS, Stewart EA, Bradley L, Marsh E, Archer D, Al-Hendy A, Petraglia F, Watts N, Gotteland JP et al.. (2022)
Linzagolix with and without hormonal add-back therapy for the treatment of symptomatic uterine fibroids: two randomised, placebo-controlled, phase 3 trials.
Lancet, 400 (10356): 896-907. [PMID:36116480]
3. Keam SJ. (2022)
Linzagolix: First Approval.
Drugs, 82 (12): 1317-1325. [PMID:35997940]
4. Niaz R, Saeed M, Khan H, Ali MA, Irshad A, Faiz M, Irshad A, Fatima F, Tunio SA, Aiman W. (2022)
Efficacy and Safety of Oral GnRh Antagonists in Patients With Uterine Fibroids: A Systematic Review.
J Obstet Gynaecol Can, 44 (12): 1279-1288. [PMID:36368594]
5. Tezuka M, Tamai Y, Kuramochi Y, Kobayashi K, Fushimi N, Kiguchi S. (2022)
Pharmacological characterization of linzagolix, a novel, orally active, non-peptide antagonist of gonadotropin-releasing hormone receptors.
Clin Exp Pharmacol Physiol, 49 (10): 1082-1093. [PMID:35690889]
6. Yan H, Shi J, Li X, Dai Y, Wu Y, Zhang J, Gu Z, Zhang C, Leng J. (2022)
Oral gonadotropin-releasing hormone antagonists for treating endometriosis-associated pain: a systematic review and network meta-analysis.
Fertil Steril, 118 (6): 1102-1116. [PMID:36283862]